Hi Sean.
Let me say that I was also a late starter w.r.t getting my Cpl/Ir/Mcc. I started my 14 atpl subjetcs in the hiring boom of 2005-2007(March 2007 to be exact). I got my MCC last February and now have a GA "job" .. no pay just free flying for which I am extremely gratefull. Did all the training modular and all of it part-time.
As a low houred wannabe and being 39 soon I've serious concerns as to whether I will ever get to the flight deck of a King Air let alone an airliner.... although I would be over the moon with any sort of paid job on a lovely plane such as the Beech (before you old school pilots jump down my throat and accuse me of calling the King Air "only a King Air").
From the outset I was perfectly content with this working your way up strategy that has existed for eternity coupled with the lower earnings as I have saved up to compensate for this during my 13 year medical career. My view is slightly different now with CTC/OXFORD etc spitting out cadets month after month and airlines mopping these up before even giving us modular guys a look.
My point is do it if you want. But you will need to pay a lot more for a further type rating AND hours on type unless you are very very lucky.
Good luck